Diastereoselective sp3‐C–H Functionalization of Arylmethyl Ketones and Transformation of E‐ to Z‐Products Through Photocatalysis

We have developed an efficient metal‐free route for the synthesis of 1,4‐enedione derivatives under microwave irradiation by reacting easily available arylmethylketones with DMSO or diphenyl sulfoxide in the presence of TBAI and persulfate. The reaction is very clean and completes within very short...

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Bibliographic Details
Published in:European journal of organic chemistry 2020-01, Vol.2020 (4), p.424-428
Main Authors: Rastogi, Gaurav K., Deka, Bhaskar, Deb, Mohit L., Baruah, Pranjal K.
Format: Article
Language:English
Subjects:
1,4‐Enediones
Arylmethylketones
C–H functionalization
Diastereoselectivity
Irradiation
Ketones
Photocatalysis
Reagents
Stereoselectivity
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Summary:We have developed an efficient metal‐free route for the synthesis of 1,4‐enedione derivatives under microwave irradiation by reacting easily available arylmethylketones with DMSO or diphenyl sulfoxide in the presence of TBAI and persulfate. The reaction is very clean and completes within very short time. All the reagents and catalysts are cheap and environmentally benign. In addition, the E‐isomer of the products can easily be transformed into the Z‐isomer by using eosin Y photocatalyst under the irradiation of white CFL. A Metal‐free synthetic route for 1,4‐enedione derivatives under microwave irradiation from the reaction of arylmethylketones with DMSO or diphenyl sulfoxide was developed. E‐isomers of the products can be transformed into Z‐isomers through visible light promoted photocatalysis.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201901415